My current Tacoma (02) was 3 years old with 19400 miles on it when I got it, so this seems like a ton of miles to me, but I know it's not really that much. I guess what I'm trying to figure is if this is worth the $$ vs. shelling out that much more for an '09...

Think about this. Go to Karl Malone and see if you can get the 0% financing on the 2009. At the very least they can get you something like 4% over 5 years (I think). Then look at what it will cost you to get a 2005 pre-owned. They will rape you on interest and the monthly will be about the same. That is why I went with new over a pre-owned.